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The 300 Dates Of A Recently Single Woman

Azelsky
7
chs / week
The average realized release rate over the past 30 days is 7 chs / week.
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Synopsis
Hello, reader. My name is Lola, and I am, once again, recently single. This is the true-ish story of my dating escapades, misadventures, and emotional roller coasters. It’s the story of how I tried (and sometimes failed) to find love, but eventually found something even better: myself. Some of these dates are real. Some have been lightly exaggerated for your entertainment (and my sanity). All names have been changed to protect the innocent, or the guilty, depending on who you ask. I’m not here to pretend I’ve got it all figured out. I’ve made mistakes, I’ve been the red flag, and I’ve also waved it like a bullfighter in stilettos. But if sharing my disasters helps you avoid your own... or at least makes you laugh until you snort, then I’ve done my job. So grab a drink, settle in, and join me as I take you through 300 dates of chaos, comedy, and, somewhere along the way, self-love. Xoxo Lola
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Chapter 1 - Love Is A Battlefield & I Was Unarmed

Ah, high school. The magical time when most people were dating everyone, kissing anyone, and occasionally losing their virginity behind the bleachers. But not me. Oh, no. My parents were having none of that.

See, my parents weren't just strict. They weren't just religious. They were in a cult. They wouldn't call it that now, but trust me. If it looks like a cult, prays like a cult, and thinks kissing before marriage is a one-way ticket to eternal damnation... it's probably a cult.

Every one of their friends had at least eight kids. Eight. My parents were practically rebels with only five. And as the oldest of those five, I was the first to face their divine doctrine of dating, which wasn't really "dating" at all.

Instead of "dating," my sister Marie (a year younger than me) and I were allowed to court.

For those of you lucky enough not to know, courting is basically "dating on nightmare mode." It's when two people are only allowed to get to know each other with a chaperone present —usually a parent with the emotional range of a security camera.

No being alone.

No hand-holding.

No kissing.

No "longing glances" (seriously, they had rules for eye contact).

And definitely no touching. Because everyone knows that one accidental brush of the fingers and suddenly "Impure Thoughts!"

Picture it: You're sitting on the living room couch with a boy you're supposed to be getting to know, and there's your mom across the room, cross-stitching Bible verses and staring at you like a lifeguard watching for a drowning toddler.

I'm honestly surprised they didn't have a spray bottle for me and my sister, like we were a pair of overzealous cats. "Hey! No romantic feelings!" Spritz.

And this was my introduction to romance. Love was a battlefield, and I was armed with nothing but a purity ring and a crushing fear of my parents' wrath. 

But being a girl in a world where women belonged to their fathers until they belonged to their husbands meant you were always being tested, judged, or prepared for a future you didn't choose.

Like the time my dad took me to a "godly family's" house, one with eight boys.

They had eight boys. Eight. A sweaty, stinky, hormonal boy band of awkwardness—and I fell right in the middle of their ages. I thought I was there to play our favorite trading card game. They thought I was some sort of prize. Or at least that's how they stared at me, like I was a rare holographic Charizard.

The whole thing was a fever dream of forced politeness. My dad and I stayed for dinner with their family —twelve people crammed around a table, passing bowls of mashed potatoes and peas while I tried to make myself invisible. I was 15, a sophomore in high school, just a walking bundle of nerves and social anxiety. The boys didn't know what to do with themselves. They kept sneaking glances at me, their cheeks going red, one of them even knocked over his cup trying to "accidentally" bump my hand.

I should've known something was off when their mom kept looking at me like she was calculating my dowry. But I was naive. I thought we were just there to hang out.

Then dinner ended. Plates were scraped, cups drained, and just as I thought I'd finally get to escape, their mom stood up and pointed at me.

"You can do the dishes."

Not a question. Not a suggestion. A command.

My dad didn't blink. He didn't say a word. He just nodded, and that was it —I was sentenced to the sink, a stranger in someone else's kitchen, scrubbing dried spaghetti off plates for a family I didn't even know. Twelve people. Twelve plates. Forks. Knives. Cups. I washed every one of them while the boys shuffled awkwardly behind me, trying to "help" by pointing out which plates were dirty.

My hands were pruny and raw from hot, soapy water. My feet ached, and my cheeks burned with embarrassment. The boys hovered, watching me like I was a zoo exhibit. Not one of them lifted a finger.

I didn't get to complain. I didn't get to say "this isn't fair" or "I don't even know you people." I just did them, because that's what a good girl does, right? Obey without question. Smile without thinking. Clean up other people's messes because... because that's just the role you've been assigned.

When we finally left, I wasn't sure if I'd just been tested, auditioned, or sacrificed. But I learned a valuable lesson that night: In a world where girls are future housewives and boys are future leaders, I was just free labor with a side of social anxiety.

My sister Marie was the tomboy with big tits. In other words, every guy's dream girl. She had boys calling at all hours, much to my parents' dismay, as if the phone was a direct line to Satan's teenage army.

And then there was me.

Super tall. Skinny as a flagpole. Awkward with a capital A. Like, painfully awkward. I looked like a baby giraffe trying to roller skate, and my social skills were... let's just say "under construction."

(As an adult, I know I have ADHD and Autism. But back then, I just thought I was weird. Weird with a side of cheese facts, because, oh yes, I could name way too many cheese facts.)

I was the kid who got bullied in elementary school. The one who sat alone with a book and a quiet ache in her chest. I had zero self-esteem, zero self-worth, and a desperate hope that maybe, just maybe, a relationship would fix all of that. Because nothing says "healthy emotional foundation" like "please let someone else make me feel like I matter."

(Spoiler alert, because I already gave away the ending in the synopsis: No one can fix you but you.)

Sorry, my ADHD squirrel brain will occasionally throw wisdom at you, reader. You're welcome.

But back to the "love story."

The first boy who ever looked twice at me? Freshman year. It was an immediate no from me. Poor kid.

But then there was Bohdi.

Husky, awkward, and quiet —basically my perfect type, because nothing screams "soulmate" like shared social anxiety. He had a best friend named Greg, who was the loud, obnoxious type —one of those guys who thinks he's hilarious because he knows five inappropriate jokes.

The first time I met Greg, he leaned over with a grin and asked,

"Hey, you wanna meet my best friend Richard?" he asked, wiggling his eyebrows like a cartoon pervert.

Now, because I was innocent as a Disney princess and roughly as clueless, I didn't know "Richard" was slang for a penis. I just thought he was weird. (Narrator: He was. He very much was.)

But Bohdi? He was sweet. He was gentle. He was... staring at his shoes more than he ever looked at me. But he was the first boy who didn't immediately run the other way when I started talking about cheese facts.

Bohdi asked me to be his girlfriend right before summer break of my sophomore year. I was over the moon. Or I would've been, if I actually knew what being someone's girlfriend meant.

But here's the thing about high school relationships when your parents are in a cult: They aren't relationships. They're just supervised awkwardness. You don't even get to talk without a chaperone. So our entire romance consisted of me sneaking onto our home phone every night —an ancient cordless landline, because this was pre-cellphones, back in the era of "don't pick up, I'm expecting a call!"

I would call him. Every. Single. Night.

And my sister Marie? Oh, she was right there on the other line, phone on mute, listening like a secret agent. She would feed me lines, because I had all the conversational charm of a nervous giraffe.

Without her, I would've sounded like a malfunctioning robot.

"How was... your... life?"

"Stop it. Ask him about his day!" she'd whisper.

"You laugh like a dying seal. Soft, not scary!

For the love of God, stop talking about cheese facts!"

And for two whole months, this was our "relationship." Me calling. Him answering. Stilted conversation punctuated by my sister's whispered coaching. I would've been lost without her.

But Bohdi? He never called me. Not once. Not even a "missed call." Not even an "oops, wrong number."

At first, I let it slide. Then I got annoyed. Then I became an absolute menace.

"Why don't you ever call me?" I asked.

"Oh, I don't know," he mumbled.

"You should call me. You never call me. Call me tomorrow."

Spoiler: He didn't. He never did.

Finally, after two months of this one-sided "relationship," I had enough. I gave him an ultimatum (because nothing says "healthy communication" like a barely 16-year-old demanding respect).

"I'm not calling you again. If you want to keep this going, you have to call me."

And I waited. And waited. And... nothing.

Summer ended, school started, and I assumed we were done. Until one day, Bohdi's loudmouth best friend Greg cornered me in the hallway.

"Hey, what happened with you and Bohdi?" he asked.

I shrugged. "He never called me back."

"Wait, so... are you guys broken up?"

"Not that I know of. He just never called me."

Greg's eyes went wide, like I'd just dropped the juiciest piece of high school drama since someone found out Jennifer stuffed the left side of her bra. He scampered off, presumably to tell Bohdi I'd publicly declared our tragic "non-breakup."

And that was it. Bohdi never spoke to me again. He just... disappeared.

Technically, we never broke up. So by the laws of awkward high school logic, we might still be dating to this day —twenty-something years later.

Hey Bohdi, just in case you didn't know… I'm single again. Call me. Or, you know, actually call me this time.